Herbicidal 2-halo-N-(cyclicimidoalkylene)-substituted acetanilides

ABSTRACT

Herbicidal N-(acyl-tertiary-amidoalkyl)-2-halo-substituted acetanilides.

United States Patent Olin 51 Sept. 23, 1975 [54] HERBICIDAL [58] Fieldof Search 71/118, 95, 98

2-HALO-N-(CYCLICIMIDOALKYLENE)- SUBSTITUTED ACETANILIDES 5 ReferencesCited [75] Inventor: John F. Olin, Ballwin. MO. UNITED STATES PATENTS[73] Assignee: Monsanto Company, St. Louis, Mo. 3.631847 1/1972 01in .171/118 8 12 k' e Sept. 2 ,1973 3,7 0090 /1973 A lbd 71/l15 [21] Appl.No.: 400,272 Primary ExaminerJames 0. Thomas, Jr

Related Application Data Attorney, Agent, or Firm--William I. Andress[62] Division of Ser. No. 148.892, June 1, 1971, Pat, No.

3.769301. [57] ABSTRACT H b"d1 N- 1-t t' 'd'1k1-2-h1- 52 U.S. Cl. 71/95;71/92; 71/93; i i j acetanilidgcy er my M y a 0 [51] Int. Cl A0ln 9/2222 Claims, N0 Drawings H ERBICIDAL 2-HALO-N-(CYCLICIMIDOALKYLENE)-SUBSTITUTED ACETANILIDES This is a division of application Ser. No.148,892. filed June 1, 1971 now US. Pat. No. 3,769,301.

This invention relates to novel N-(acyl-tertiaryamidoalkyl)acetanilideswhich are useful as herbicides and to methods of preparing them. Moreparticularly, the invention relates to herbicidally activeN-(acylsubstituted amidoalkyl)acetanilides and N- acylimidoalkylaeetanilidcs. The invention also relates to herbicidal compounds and tomethods of inhibiting or preventing the growth of plants.

The term plants is used herein to include germinant seeds, emergingseedlings and established vegetation, including the roots andabove-ground portions.

The novel compounds of the present invention are represented by theformula wherein:

R and R are hydrogen, alkyl or alkoxy having at least I and not morethan 10 carbon atoms and can be like or unlike,

R is hydrogen, alkyl or alkoxy having at least I and not more than 10carbon atoms, N or halogen,

R is hydrogen, alkyl, alkenyl, alkynyl, alkoxy,

alkythio, polyalkoxy, polyalkylthio, alkoxyalkyl, alkylthioalkyl,polyalkoxyalkyl, polyalkylthioalkyl, haloalkyl, hydroxyalkyl,mercaptoalkyl, haloalkenyl, oxoalkyl, alkenyloxyalkyl, alkenylthioalkyl,each of a maximum of 18 carbon atoms; cycloalkyl having at least 3 and amaximum of 6 carbon atoms; aryl, aryloxyalkyl, arylthioalkyl,trifluoromethyland haloaryl, trifluoromethyland haloaryloxyalkyl,trifluoromethyland haloarylthioalkyl, arylalkyl, nitroaryl,nitroarylthioalkyl, and nitroarylalkyl having at least 6 and not morethan 24 carbon atoms; amino or mono and dialkylamino, monoarylamino,mono(haloaryl)amino, mono(trifluoromethylaryl)amino, and alkylalkoxyamino having a maximum of carbon atoms,

R is alkyl, alkenyl, aryl or alkaryl having a maximum of l8 carbonatoms, or R and R are combined to form an alkylene or alkenylene bridgehaving at least 2 and not more than 5 carbon atoms, or a phenylenegroup,

X is chlorine, bromine or iodine,

m is an integer of l or 2, and n is an integer of 0 to 2 inclusive.

Unless otherwise indicated, alkyl and alkoxy" are used generically toinclude primary, secondary, and tertiary groups.

Representative compounds of the present invention include those in whichthe groups ofthe above formula have the following identities:

R and R hydrogen, methyl. ethyl, propyl, isopropyl, n-butyl, primaryisobutyl, secondary isobutyl, tertiary butyl, n-amyl, branch chainamyls, the normal and branched hexyls, heptyls, octyls, nonyls, anddecyls, methoxy. ethoxy. propoxy, butoxy. pentyloxy. heptyloxy,nonyloxy;

R hydrogen, chlorine, bromine, fluorine, iodine, nitro and the alkyl andalkoxy groups of R and R;

R hydrogen, methyl. ethyl, propyl, isopropyl, n butyl, isobutyl,tertiary butyl, the normal and branched amyls, hexyls. heptyls, octyls,nonyls, decyls, dodecyls, tetradecyls, hexadccyls and octadecyls;chloromethyl. bromopropyl, iodobutyl, fluorohexyl, hydroxyethyl,dihydroxypropyl; the alkoxy, alkenyl, oxoalkyl, alkoxyalkyl and alkynylgroups corresponding to the aboveenumerated alkyl groups; phenyl, tolyl,naphthyl, phenoxy, benzyl, phenoxyalkyl; halophenoxyalkyls; ethylene,trimcthylene, tetramethylene; and the like.

R the alkyl, alkenyl. alkynyl, aryl and alkaryl groups of R.

When R and R are combined as a polymethylene bridge between the nitrogenatom and the carbonyl carbon atom and n is 0, lactamyl radicals areformed. These include 2pyrrolidinon-l-yl or (2-oxotetramethylene imino),Z-piperidinon-l-yl or (2- oxopentamethylene imino) and2-oxo-hexamethylene imino. When n is l, R and R can combine to formcyclic imides including phthalimides.

The preferred compounds of the present invention are those in which bothR and R are ethyl and more particularly the compounds in which they arein the ortho positions.

The novel compounds of the present invention in which m is l areprepared by the reaction of a substituted methylenearylamine of the typedisclosed and claimed in copending application Ser. No. 625,020 filedMar. 22, 1967, with an appropriately substituted amide or imide to formthe corresponding N- (anilinomethyl) amide or imide. The intermediateamide or imide is then haloacetylated with a haloacetylhalide to providethe compounds under consideration.

The novel compounds in which m is 2 are readily prepared by thehaloacetylation of an N-(substitutedphenyl)-N'-acyl-N'-hydrocarbyl-ethylenediamine. The ethylenediaminederivatives used as starting materials for such reactions can be readilyprepared in conventional manners by the alkylation of a substitutedaniline with an alkylating agent such as an N(2-chloroethyl)-alkylamide, an N-2-(hydroxyethyl)-alkylamide or an N-acyl aziridine.

The invention will be more clearly understood by reference to thefollowing detailed description of specific examples thereof. In theseexamples and throughout the specification, all proportions are expressedin part by weight unless otherwise indicated.

EXAMPLE 1 N-( 2,6-Diethylanilinomethyl )-N-methylacetamide About lOOparts of N-methylacetamide were charged into a suitable reaction vesseland about 100 parts of 2% sodium methoxide suspension indimethylformamide were added. The reaction was exothermic and thetemperature of the reaction mixture rose from about 24C to about 30C.Then about 160 parts of 2,6- diethyl-N-methyleneaniline were addedresulting in an additional rise in temperature to about 44C. Thereaction mixture was maintained at this temperature with continuedagitation for about 7 hours. With continued stirring it was permitted toreturn to room temperature over a period of about 16 hours. About 3parts of acetic acid were added, then about 200 parts water and themixture vigorously agitated. About 150 parts of benzene were added toaid in the separation of the mixture into an oil layer and a waterlayer. The water layer was discarded and the oil layer washed with anadditional 200 parts water containing one part acetic acid, dried overmagnesium sulfate and vacuum distilled. A straw colored liquididentified as N2,o-diethylanilinomethyl- N-methyl acetamide wasobtained.

Calcd for C H N oz Found:

EXAMPLE 2 'N COCH 3 COCHzCl About 72 parts ofN-(2,6-dimethylanilinomethyl)-N- methylacetamide obtained in accordancewith the procedure of Example 1 were dissolved in about 100 grams oftoluene and introduced into a suitable reaction vessel to which about 40parts of 2,6-lutidine were added. The mixture was chilled with carbondioxide-acetone and while being vigorously agitated about 40 parts ofchloroacetyl chloride in 70 parts of benzene were added over a 15 minuteperiod with the temperature of the reaction mixture being maintainedbetween C and 30C. With continued agitation, the reaction mixture waspermitted to warm to room temperature. About 100 parts of water werethen added and the mixture separated into an oily fraction and anaqueous fraction. The aqueous fraction was discarded and the oilyfraction washed twice with 150 parts of water at a temperature of about35C. The reaction mixture was then vacuum evaporated to substantialdryness and about 100 parts methylcyclohexane added to the residuefollowed by the addition of about 15 parts benzene to provide ahomogeneous solution. The product crys- LII tallized from the solutionupon standing and was removed from the liquid phase by filtration. Theprecipitate was washed with a mixture of methylcyclohexane and benzeneand then air dried. After recrystallization from a benzenehexanemixture, a cream colored product was obtained.

Calc'd for C H CIN O C. 6| .83 H. 7.46 Cl. ll.4l-

N. 9.0l C. 61.68 H. 7.47 C]. ll.48

A mixture of about 30 parts of 2,6-diethyl-N- methyleneaniline, 20 partsof succinimide and parts of dimethyl formamide were heated at atemperature of about 95C for 18 hours in a suitable reaction ves-.

sel. The reaction mixture was then vacuum evaporated to provide aresidue containing N-(2,6- diethylanilinomethyl)-succinimide. Theresidue was dissolved in about parts of toluene and about 30 parts2,6-lutidine were added. The mixture was cooled to about l0C and about23 parts of chloroacetyl chloride were added incrementally over a periodof 20 minutes while maintaining the temperature of the reaction mixturebetween about lOC and 5C. This resulted in the formation of a heavyprecipitate. The reaction mixture was then cooled to about 0C andmaintained at that temperature for about one hour, at the end of whichtime the precipitate was removed from the dark mother liquor. Theprecipitate was washed with dilute hydrochloric acid, water and thenwith toluene. The precipitate was then recrystallized from amethylcyclohexane-ethyl acetate mixture to obtain a gray powder having amelting point of l46l47C.

Calcd for C H CIN O C. 60.62 H, 6.28 CI. 10.53

2-chloro-2 ',6 '-diethyl-N- 2-pyrrolidinonl yl )methyl]acetanilide About40 parts of N-(2,6-diethylanilinomethyl)-2- pyrrolidinone were dissolvedin about 100 parts toluene and about 30 parts 2,6-lutidine were added tothe solution contained in a suitable reaction vessel. The mixture wasthen cooled to about 30C with continuous agitation. About 23 parts ofchloroacetyl chloride dissolved in about 80 parts toluene were addedover a 15 minute period while maintaining the temperature of the mixturebetween 20 and 30C. After the addition was complete, the reactionmixture was permitted Calc'd for C,7H23CIN,O: C. 63.25 H. 7.18 Cl, 10.98Found: C, 63.36 H. 7.33 CI. 11.02

EXAMPLE N-(2,6-diethylanilinomethyl)-N,N,N- trimethyloxamide CH 3 O O CHAbout 650 parts of N,N',N'-trimethyloxamide and about 4 parts ofpotassium hydroxide pellets were introduced into a suitable reactionvessel and about 800 parts of 2,6-diethylphenylazomethine were added,followed by the addition of about 5 parts of a 25% solution of sodiummethoxide in methanol. The reaction started slowly and the temperaturerose from room temperature to about 50C. in minutes, followed by a dropin temperature to about 45C. The mixture was subsequently heated toabout 100C. with continued stirring and allowed to cool to roomtemperature (about 23C.). The resulting honey-like syrup which containedsome unreacted pellets of sodium hydroxide was dissolved in 2.500 partsof methylcyclohexane and acidified with about 10 parts of acetic acid.Upon stirring the reaction mixture. the product crystallized to formcolorless granules which were filtered and washed twice with 1.200 partsof methylcyclohexane. The product was finally washed 3 times with 1,500parts of water and air dried. The product thus obtained had a meltingpoint of 73--73.3C.

This compound and related compounds having 2 adjacent carbonyl groupscan be readily haloacetylatcd to form compounds of the present inventionin which n is 2.

EXAMPLES 6 THROUGH 41 The following compounds are also prepared bysubstantial repetition of the general procedures set forth in theforegoing Examples.

6. 2-chloro-2,6'-dimethylN-(succinimidomethyl- )acetanilide 7.2-chloro2',6-dimethyl-N-(succinimidoethyl- )acetanilide 8.2-bromo-2-ethyl-6'-methyl-N-(succinimidoethyl- )acetanilide 9.2-iodo-2',6-diethyl-N-(succinimidomethyl- )acetanilide l0.2-bromo-2',6'-diethyl-N-(succinimidomethyl- )acetanilide 1 1.2-chloro2',6'-diethyl-N- (maleimidomethyl)acetanilide 12.2-chloro-2',6'-dimethyl-N- (maleimidomethyl)acetanilide 13.2-chloro-2',6-dimethyl-N-( maleimidoethyl- )acetanilide 14.2-bromo-2ethyl-6'-methyl-N-(maleimidoethyl- )acetanilide l5.(maleimidomethyl)acetanilide l6. 2-bromo-2 ',6-diethyl-N-(maleimidomethyl)acetanilide 17.2-chloro-2',6-diethyl-N-(citraconimidomethyl- )acetanilide 18.2-chloro-2',6'-dimethy1-N-(eitraconimidomethyl)acetanilide 19.2-chloro-2',6-dimethyl-N-(citraconimidoethyl- )acetanilide 20.2-bromo-2-ethyl-6'-methyl-N-(citraconimidoethyl)acetanilide 21.(itaconimidomethyl)acetanilide 22. 2-bromo-2',6'-diethyl-N-(itaconimidomethyl)acetanilide 23l(N-chloroacetyl-Z',6'-diethylanilinoethyl)-2- pyrrolidinone 24.2-chloro-2 ,6 -diethyl-N-[ Z-piperidinonl yl)methyl]acetanilide 25.2-chloro-2',6 '-diethyl-N-( 2-piperidinon-l ylethyl )acetanilide 26.2-chloro-2',6'-diethyl-N-(2-oxo-hexamethyleneiminomethyl)-acetanilide27. 2-chlor0-2',6'-diethyl-N-(2-oxohexamethyleneiminoethyl)-acetanilide2-iodo-2 ',6'-diethyl-N- 28. 2-chloro-N-(acetamido-ethyl)-2',6-diethylacetanilide '29.2-chloro-2,6'-diethyl-N-(N-methyldichlorobenzamidomethyl acetanilide 30.2-chloro-2,6'-dicthyl-N-(N-methyldichlorobenzamidoethyl acetanilide '31.2-chloro-2',6-diethyl-N-(N- ethylallylamido)methyl acetanilide 32.2-chloro-2,6'-diethyl-N-(N-methyl-3- butenamidoethyl) acetanilide 33.methylformamidomethyl acetanilide 34.2-bromo-2,6'-dimethyl-N-(N-methylformamidoethyl acetanilide 35.2-chloro-2',6'-diethyl-N-(N- methylacrylamidomethyl acetanilide 36.2-chloro-2',6'-diethyl-N-(N-ethyl-3-ethoxypropionamidomethyl acetanilide37. 2-chloro-2',6'-diethyl-N-(N-methyl-beta-chloropropionamidomethylacetanilide 38. 2-chloro-2',6 '-diethyl-N-(N-propylpropionamidomethylacetanilide 39. 2-chloro-2 '-methyl-6 '-ethyl-N-( Nethylacetamidoethylacetanilide 40. 2-chloro-2,6-diethyl-N-(N-methyl crylamidomethylacetanilide 4l. 2-chloro-N-( phthalimidomethyl)2,6'- acetoxylidide I Inorder to illustrate the advantages of the present invention, thepre-emergence herbicidal ratings of representative 2-haloacetanilideswere determined in greenhouse tests in which a specific number of seedsof a number of different plants, each representing a principal botanicaltype, were planted in greenhouse flats.

A good grade of top soil was placed in aluminum pans and compacted to adepth of three-eighths to onehalf inch from the top of the pan. On thetop of the soil was placed a predetermined number of seeds of variousplant species. In the surface application the seeds were covered byoverfilling the pan with soil and striking it level. The measured amountof chemical in a suitable solvent or as a wettable powder was applied tothis surface. In the soil incorporation treatments the soil re quired tolevel fill pans after seeding was weighed into a pan, a known amount ofthe chemical applied in a solvent or as a wettable powder, the soilthoroughly mixed, and used as a cover layer for seeded pans. Aftertreatment the pans were moved into a greenhouse bench where they werewatered from below as needed to give adequate moisture for germinationand growth.

Approximately 14 days after seeding and treating, the plants wereobserved and the results recorded. The herbicidal rating was obtained bymeans of a fixed scale based on the average percent germination of eachseed lot. The ratings are defined as follows:

No herbicidal activity 1 Slight herbicidal activity 2 Moderateherbicidal activity 3 Severe herbicidal activity The pre-emergenceherbicidal activity of the alphahaloacetanilides are recorded in thefollowing table for various application rates in both surface andsoilincorporated applications.

In the table, the letter M following the rate of application indicatesthat the herbicide was incorporated in the soil and the various seedsare represented by letters as follows:

metha- A Soybean l Hemp seshania B Sugar Beet J Lambsquarters C Wheat KVelvctlcaf D Rice L Brornus Tectorum E Sorghum M Panicum sppi FCncklebur N Barnyardgrass (common) G Wild Buckwheat -H Morningglory OCrahgrass Compound of Rate ExampleNo. lh./A ABCDEFGHIJKLMNO l l-ll000002-()ll33 V4 010000001000122 The data set forth in theforegoing'table clearlyillustrates that the compounds of the presentinvention are effective'herbicides and'are particularly useful in thecontrol of narrow leaf or grass weeds, even in the presence of cropsincluding soybean, sugar beet, rice and sorghum.

The herbicidal compositions of this invention including concentrateswhich require dilution prior to application contain at least one activeingredient and an adjuvant in liquid or solid form. The compositions areprepared by admixing the active ingredient with an adjuvant includingdiluents, extenders, carriers and conditioning agents to providecompositions in the form of finely-divided particulate solids, granules,pellets, solutions, dispersions or emulsions. Thus the active ingredientcan be used with an adjuvant such as a finelydivided solid, a liquid oforganic origin, water, a wetting agent, a dispersing agent, anemulsifying agent or any suitable combination of these.

The compositions of this invention, particularly liquids and wettablepowders, preferably contain as a conditioning agent one or moresurface-active agents in amounts sufficient to render a givencomposition readily dispersible water or in oil. The incorporation of asurface-active agent into the compositions greatly enhances theirefficacy. By the term surface-active agent" it is understood thatwetting agents, dispersing agents, suspending agents and emulsifyingagents are included therein. Anionic, cationic and non-ionic agents canbe used with equal facility.

Preferred wetting agents are alkyl benzene and alkyl naphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, long chainacid esters of sodium isethionate, esters of sodium s ulfosuccinate,sulfated or sulfonated fatty acid esters petroleum sulfonates,sulfonated vegetable oils,s ditertiary acetylenic glycols,polyoxyethylene derivatives oils, alkylphenols (particularlyisooctylphenol and nonylphenol) and polyoxyethylene derivatives of themono-higher fatty acid esters of hexitol' anhydrides (e.g., sorbitan).Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodiumlignin sulfonates, polymeric alkyl naphthalene sulfonates, sodiumnaphthalene sulfonate, andpolymethylene bisnaphthalenesulfonate.

Wettable powders are water-dispersiblecompositions containing one ormore active ingredients, an inert solid extender and one or more wettingand'dispersing agents. The inert solid extenders are usually of mineralorigin such as the natural clays, diatomaceous earth and syntheticminerals derived from silica and the like. Examples of such extendersinclude kaolinites, attapulgite clay and synthetic magnesium silicate.The wettable powders compositions of this invention usually contain fromabout 5 to about 95 parts of active in gredient, from about 0.25 to 25parts of wetting agent, from about 0.25 to 25 parts of dispersant andfrom 4.5 to about 94.5 parts of inert solid extender, all parts being byweight of the total composition. Where required, from about 0.1 to 2.0parts of the solid inert extender can be replaced by a corrosioninhibitor or antifoaming agent or both.

Aqueous suspensions can be prepared by mixing together and grinding anaqueous slurry of waterinsoluble active ingredient in the presence ofdispersing agents to obtain a concentrated slurry of very finelydividedparticles. The resulting concentrated aqueous suspension ischaracterized by its extremely small particle size, so that when dilutedand sprayed, coverage is very uniform.

Emulsifiable oils are usually solutions of active ingredient inwater-immiscible or partially water-immiscible solvents together with asurface active agent. Suitable solvents for the active ingredient ofthis invention inelude hydrocarbons and water-immiscible ethers, estersor ketones. The emulsifiable oil compositions generally contain fromabout 5 to 95 parts active ingredient, about 1 to 50 parts surfaceactive agent and about 4 to 94 parts solvent, all parts being by weightbased on the total weight of emulsifiable oil.

Granules are physically stable particulate compositions comprisingactive ingredient adhering to or distributed through a basic matrix ofan inert, finelydivided particulate extender. In order to aid leachingof the active ingredient from the particulate, a surface active agentsuch as those listed hereinbefore can be present in the composition.Natural clays, pyrophyllites, illite and vermiculite are examples ofoperable classes of particulate mineral extenders. The preferredextenders are the porous, absorptive, preformed particles such aspreformed and screened particulate attapulgite or heat expanded,particulate vermiculite, and the finelydivided clays such as kaolinclays, hydrated attapulgite or bentonitic clays. These extenders aresprayed or blended with the active ingredient to form the herbicidalgranules.

The granular compositions of this invention generally contain from about5 parts to about 30 parts by weight of active ingredient per 100 partsby weight of clay and to about parts by weight of surface active agentper 100 parts by weight of particulate clay. The preferred granularcompositions contain from about parts to about parts by weight of activeingredient per 100 parts by weight of clay.

The compositions of this invention can also contain other additaments,for example fertilizers, herbicides, other pesticides and the like usedas adjuvants or in combination with any of the above-describedadjuvants. Chemicals useful in combination with the active ingredientsof this invention include for example triazines, ureas, carbamates,acetamides, acetanilides, uracils, acetic acids, phenols,thiolcarbamates, triazoles,

2-methoxy-4-ethylamino-6-isopropylamino-s-triazine2-chloro-4-ethylamino-6'isopropylamino-s-triazine2-chloro-N,N-diallylacetamide 2-chloroallyl diethyldithiocarbamateN'-(4-chlorophenoxy) phenyl-N,N-dimethylurcal,l-dimethyl-4,4'-bipyridinium dichloride isopropylN-(3-chlorophenyl)carbamatc 2,2-dichloropropionic acidS-2,3-dichloroallyl N,N-diisopropylthiolcarbamate2-methoxy-3,o-dichlorobenzoic acid 2,6-dichlorobenzonitrileN,Ndimethyl-2,Z-diphenylacetamide 6,7-dihydrodipyrido( l ,2-a:2,l'-c)-pyrazidiinium salt 3-(3,4-dichlorophenyl)-1,1-dimethylurea4,6-dinitro-o-sec-butylphenol 2-methyl-4,6-dinitrophenol ethylN,N-dipropylthiolcarbamate 2,3,6-trichlorophenylacetic acidS-bromo-3-isopropyl-6-methyluracil 3-( 3 ,4-dichlorophenyl l -methoxy- 1methylurea 2-methyl4-chlorophenoxyacetic acid 3-(p-chlorophenyl )-l l-dimethylurea l-butyl-3-(3,4-dichlorophenyl)-l-mcthylurea N- lnaphthylphthalamic acid l,1'-dimethyl-4,4'-bipyridinium salt2-chloro-4,6-bis(isopropylamino)-s-triazine2-chloro-4,6-bis(ethylamino)-s-triazine 2,4-dichlorophenyl-4-nitrophenylether alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-dipropylp-toluidineS-propyl dipropylthiolcarbamate 2,4-dichlorophenoxyacetic acidN-isopropyl-2-chloroacetanilide2,6'-diethyl-N-methoxymethyl-2-chloroacetanilide monosodium acidmethanearsonate disodium methanecarsonate N-( l l -dimethylpropynyl)-3,5-dichl0robenzamide Fertilizers useful in combination with theactive ingredients include for example ammonium nitrate, urea, potash,and superphosphate. Other useful additaments include materials in whichplant organisms take root and grow such as compost, manure, humus, sandand the like.

When operating in accordance with the present invention, effectiveamounts of the acetanilides are applied to the plants, or to soilcontaining the plants, or are incorporated into aquatic media in anyconvenient fashion. The application of liquid and particulate solidcompositions to plants or soil can be carried out by conventionalmethods, e.g., power dusters, boom and hand sprayers and spray dusters.The compositions can also be applied from airplanes as a dust or a spraybecause of their effectiveness at low dosages. The application ofherbicidal compositions to aquatic plants is usually carried out byadding the compositions to the aquatic media in the area where controlof the aquatic plants is desired.

The application of an effective amount of the compounds of thisinvention to the plant is essential and critical for the practice of thepresent invention. The exact amount of active ingredient to be employedis dependent upon various factors, including the plant species and stageof development thereof, the type and condition of soil, the amount ofrainfall and the specific acetanilide employed. In non-selectivepre-emergence treatments, the compounds of this invention are usuallyapplied at an approximate rate of from 1 to 25 pounds per acre. lnselective preemergencc application to the plants or to the soilcontaining a dosage of from 0.05 to about pounds of acetanilidc per acreis usually employed. Lower or higher rates may be required in someinstances. One skilled in the art can readily determine from thisspecification, including the examples. the optimum rate to be applied inany particularly case.

The term soil is employed in its broadest sense to be inclusive of allconventional soils as defined in Websters New International Dictionary,Second Edition,, Unabridged (1961). Thus the term refers to anysubstance or media in which vegetation may take root and grow, andincludes not only earth but also compost, manure, muck, humus, sand andthe like, adapted to support plant growth.

Although the invention is described with respect to specificmodifications, the details thereof are not to be construed aslimitations except to the extent indicated in the following claims.

What is claimed is:

l. A herbicidal composition comprising an adjuvant and an effectiveamount of a compoundof the formula R and R are hydrogen, alkyl or alkoxyhaving at least 1 and not more than carbon atoms and can be like orunlike,

R is hydrogen, alkyl or alkoxy having at least 1 and not more than 10carbon atoms, N0 or halogen and i R and R are combined to form analkylene or alkenylene bridge having at least 2 and not more than 5carbon atoms, or a phenylene group,

X is chlorine, bromine or iodine,

m is an integer of l or 2, and n is an integer of O to 2 inclusive.

2. A composition of claim 1 wherein R and R are alkyl and are in the 2and 6 position.

3. ,A composition of claim 2 wherein R and R are ethyl.

4. A composition of claim 1 wherein m is 1.

5. A composition of claim 4 wherein n is 0.

6. A composition of claim 4 wherein n is 1.

7. A composition of claim 5 wherein R and R are combined to form aphenyl group or a polymethylene bridge having at least 2 and not morethan 5 carbon atoms.

8. A composition of claim 6 wherein R and R are combined to form aphenyl group or a polymethylene bridge having at least 2 and not morethan 5 carbon /C CH X (CH2) N C n R 2 1 I,

wherein:

R and R are hydrogen, alkyl or alkoxy having at least 1 and not morethan 10 carbon atoms and can be like or unlike,

R is hydrogen, alkyl or alkoxy having at least 1 and not more than 10carbon atoms, N0 or halogen and R and R are combined to form an alkyleneor alkenylene bridge having at least 2 and not more than 5 carbon atoms,or a phenylene group,

X is chlorine, bromine or iodine,

m is an integer of l or 2, and n is an integer of 0 to 2 inclusive.

13. A method of claim 12 wherein R and R are alkyl and are in the 2 and6 positions.

14. A method of claim 13 wherein R and R are ethyl.

15. A method of claim 12 wherein m is l.

16. A method of claim 15 wherein n is O.

17. A method of claim 15 wherein n is 1.

18. A method of claim 16 wherein R and R are combined to form a phenylgroup or a polymethylene bridge having at least 2 and not more than 5carbon atoms.

19. A method of claim 17 wherein R and R" are combined to form a phenylgroup or a polymethylene bridge having at least 2 and not more than 5carbon atoms.

20. A method of claim 12 wherein the compound is2-chloro-N-(N-methylacetamido)methyl-2',6'- diethylacetanilide.

21. A method of claim 12 wherein the compound is2-chloro-2',6'-diethyl-N-(succinimidomethyl)acetanilide.

22. A method of claim 12 wherein the compound is l-(N-chloroacetyl-2',6'-diethylanilinomethyl-2- pyrrolidinone.

1. A HERBICIDAL COMPOSITION COMPRISING AN ADJUVANT AND AN EFFECTIVEAMOUNT OF A COMPOUND OF THE FORMULA
 2. A composition of claim 1 whereinR and R1 are alkyl and are in the 2 and 6 position.
 3. A composition ofclaim 2 wherein R and R1 are ethyl.
 4. A composition of claim 1 whereinm is
 1. 5. A composition of clAim 4 wherein n is
 0. 6. A composition ofclaim 4 wherein n is
 1. 7. A composition of claim 5 wherein R3 and R4are combined to form a phenyl group or a polymethylene bridge having atleast 2 and not more than 5 carbon atoms.
 8. A composition of claim 6wherein R3 and R4 are combined to form a phenyl group or a polymethylenebridge having at least 2 and not more than 5 carbon atoms.
 9. Acomposition of claim 1 wherein the compound is2-chloro-N-(N-methylacetamido)methyl-2'',6''-diethylacetanilide.
 10. Acomposition of claim 1 wherein the compound is2-chloro-2'',6''-diethyl-N-(succinimidomethyl)acetanilide.
 11. Acomposition of claim 1 wherein the compound is1-(N-chloroacetyl-2'',6''-diethylanilinomethyl-2-pyrrolidinone.
 12. Aherbicidal method which comprises applying an effective amount of acompound of the formula
 13. A method of claim 12 wherein R and R1 arealkyl and are in the 2 and 6 positions.
 14. A method of claim 13 whereinR and R1 are ethyl.
 15. A method of claim 12 wherein m is
 1. 16. Amethod of claim 15 wherein n is
 0. 17. A method of claim 15 wherein nis
 1. 18. A method of claim 16 wherein R3 and R4 are combined to form aphenyl group or a polymethylene bridge having at least 2 and not morethan 5 carbon atoms.
 19. A method of claim 17 wherein R3 and R4 arecombined to form a phenyl group or a polymethylene bridge having atleast 2 and not more than 5 carbon atoms.
 20. A method of claim 12wherein the compound is2-chloro-N-(N-methylacetamido)methyl-2'',6''-diethylacetanilide.
 21. Amethod of claim 12 wherein the compound is2-chloro-2'',6''-diethyl-N-(succinimidomethyl)acetanilide.
 22. A methodof claim 12 wherein the compound is1-(N-chloroacetyl-2'',6''-diethylanilinomethyl-2-pyrrolidinone.